Shirts! When to tuck and when not to?

Hello all,

I've been giving this some serious thought recently (maybe too much) to the point I end up doubting my own style!

In almost all cases in the past I have worn my shirts tucked into my trousers, but now I'm wondering if I shouldn't. With a suit it's a given to tuck, but with say a flannel button down shirt for casual wear with a pair of chinos? Or a blue oxford shirt with some tailored shorts and loafers?

It depends where you're wearing the shirt, the type of shirt, what you're wearing with the shirt, etc. For example, flannel shirts normally don't suit being tucked in because they are often worn in colder months as part of a worker style outfit, whereas oxford shirts are often worn for more formal occasions or in warmer times and should probably be tucked in. Personally I wear flannel and denim shirts untucked, oxford tucked in, and then things like chambray and print shirts depend on the occasion, the rest of the outfit etc.

Looks great when styled / wearing a suit, but his casual attire is dreadful

No way I think his casual attire these days is the best its ever been. Those images are old where he tried far too hard but he rocks the basic RRL and Dior jeans to perfection with a solid pair of boots or running shoes.

When smart, always tuck. Smart gear, with untucked shirt simply looks unkept and bad mannered. When casual, the field is more open, and you never tuck a short sleeved shirt.

The way I personally dress is that the line goes somewhere in the middle of smart casual (business casual is always tucked). Smart casual with tie, tucked. Smart casual without tie, there's room for untucked.

As I'm well into my 30's now, I find that most of my peers wear untucked shirts to hide the fact that they've got a bit of a gut going.